Methylamine → (βS)-β-Hydroxy-N-methyl-2-thiophenepropanamide

HRID 730953Notes

Reaction equation

HRID 730953 reaction equation
[OH:1][C@H:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[CH2:3][C:4](OC)=[O:5].[CH3:13][NH2:14]>>[CH3:13][NH:14][C:4](=[O:5])[CH2:3][C@H:2]([OH:1])[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 10397541methyl (3S)-3-hydroxy-3-(thiophen-2-yl)propanoate

Product 1

HCID 10261821(βS)-β-Hydroxy-N-methyl-2-thiophenepropanamideYield 88%

Conditions

Temperature
60 °C

Procedure

115 g of methyl (3S)-3-hydroxy-3-(2-thienyl)propanoate are initially charged and admixed with 618 ml of a 2 molar methanolic methylamine solution. This mixture is stirred at 60° C. for 4 h, cooled and then concentrated under reduced pressure. In this way, 118 g of N-methyl-(3S)-3-hydroxy-3-(2-thienyl)propanamide (purity 86%; 88% of theory) are obtained. The crude product may be used in the next stage or else recrystallized from methylene chloride and hexane. This delivered 93 g of N-methyl-(3S)-3-hydroxy-3-(2-thienyl)propanamide (76% of theory) as white crystals. As an alternative, the purification may also be done by distillation.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b1a44c8c5964c63a47707f7bbe490bc
Source dataset
uspto-grants-2009_09
Patent number
US07582776B2

Reaction notes

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